The present invention relates to novel poly (phosphonoaryl acetylene) having an aryl group substituted with a phosphono group or a salt thereof, a chiral sensor using the same and an optical resolution using the same. The Poly (phosphonoaryl acetylene) or the salt thereof of the invention is stereoregular, exhibits circular dichroism in the presence of an optically active substance, is an excellent material in water solubility and is useful as the chiral sensor and optical resolving reagent.
As substances having optical asymmetry, a number of substances have been known such as those having asymmetric carbons and molecular asymmetry. These substances have been widely used in the industry as functional materials such as optical resolving reagents, liquid crystal materials, chiral sensors, non-linear optical materials and the like.
Among these asymmetric molecules, polymer substances having molecular asymmetry have been recently noticed, and for example, poly (triphenyl methyl methacrylate) (Japanese Patent Laid-Open No. 106907/1981) having a helix structure and high optical rotation, optically active polyacrylate amide derivatives (Japanese Patent Laid-Open No. 167708/1981) and the like have been known.
Also the present inventors previously-have found that the polymer of (4-carboxyphenyl) acetylene exhibits the splitting type of induced circular dichroism (ICD) against optically active amine and amino alcohol in an organic solvent such as dimethylsulfoxide (DMSO) (Japanese Patent Laid-open No. 176243/1997). These substances were useful as chiral sensors and optical resolving reagents with this unique nature. However, a large amount of optically active substance is required for manifestation of ICD in the organic solvent and types of amino acids which manifest ICD in water are limited. Thus, development of water soluble polymers has been desired, which more supersensitively respond to chirality of more broad range of optically active substances.
The present invention provides a water soluble polymer which more supersensitively responds to chirality of more broad range of optically active substances.